Your step-by-step retirement checklist.

1Picture your retirement

Your lifestyle largely determines how much money you will need, so start with the vision, not the spreadsheet. How will you spend your time? Where will you live? Will you support family members? Writing down real answers turns a vague hope into a plan you can actually fund.

• Write down how you want to spend your time, and what you're most excited (and worried) about.
• Decide where you plan to live — and whether a move, downsize, or renovation is coming.
• If you'll carry a mortgage, plan the financing while you're still employed (it's much easier to qualify).
• Think about purpose and social connection: hobbies, volunteering, and the work relationships you'll want to keep.

2Estimate your retirement expenses

Break spending into three buckets: needs (essential living expenses), wants (travel, hobbies, dining), and wishes (gifts and legacy). Many retirees are surprised to find spending goes up early in retirement, especially on travel and health care your employer used to cover.

• Review 6–12 months of card and bank statements to learn what you actually spend today.
• Build an annual budget for basic living expenses (needs).
• Add a stretch budget for discretionary spending (wants) and one-time items like cars and roofs.
• List the employer benefits you'll lose and what replacing them will cost.
• Try living on your projected retirement budget for a year before you retire — a real-world dress rehearsal.

Helpful reading: How Much Do You Really Need to Retire?

3Identify your income sources

Add up everything that will replace your paycheck: Social Security, any pension or annuity, part-time work, rental income — then compare it to your expense estimate. The gap is what your portfolio has to fund. This single equation drives most retirement decisions: spending − guaranteed income − work income = required portfolio income.

• Pull your benefit estimate from your SSA statement at ssa.gov, and choose a claiming strategy.
• If you have a pension, compare distribution options (lump sum vs. single life vs. joint-and-survivor).
• Total your guaranteed annual income — and, for couples, recompute it assuming one spouse passes away.
• Inventory every account: tax-deferred (401(k)/IRA), tax-free (Roth, HSA), and taxable.
• Subtract income from spending to find the annual amount your portfolio must produce.

Run the numbers: Social Security Optimizer · Retirement Readiness Calculator

4Understand your risks

A modern retirement can last 30+ years. The big risks are outliving your money, inflation, a bad market in your first few years of withdrawals (sequence-of-returns risk), and the early loss of a spouse. You can't eliminate them, but you can plan for them.

• Set aside a liquidity bucket covering the first 1–2 years of expenses so you never sell into a downturn.
• Revisit your asset allocation for the spending phase — not the saving phase — of life.
• Stress-test the plan: a first-year market drop, higher inflation, a health shock, the loss of a spouse.
• Review insurance: life, liability, home/auto — and decide what you'll self-insure.

Helpful reading: Sequence of Returns: The Risk No One Warned You About

5Plan health care & long-term care

Health care is often one of the largest retirement expenses. Medicare begins at 65 — if you retire earlier you'll need bridge coverage — and Medicare doesn't cover everything, notably dental, vision, and long-term care. Enrollment windows matter: missing them can mean lifelong premium penalties.

• If retiring before 65, price bridge coverage (COBRA vs. ACA marketplace — and whether managing income qualifies you for subsidies).
• Learn your Medicare choices: Original Medicare + Medigap vs. Medicare Advantage.
• Check whether your income will trigger IRMAA surcharges — and whether Form SSA-44 applies after a life change like retirement.
• Decide how you'll handle long-term care: self-fund, insure, or a hybrid — and tell your loved ones your wishes.
• Plan how you'll spend HSA dollars, and use FSA dollars before you lose them.

Run the numbers: Healthcare Cost Estimator · Reading: Medigap vs. Medicare Advantage

6Build your retirement paycheck

Decide how money will actually reach your checking account each month: which account is the spending hub, how often it's refilled, and where the first five years of income come from. A clear "paycheck" system is the difference between a plan on paper and a plan you can live on.

• Choose a primary spending account and route Social Security/pension deposits into it.
• Consider turning off dividend reinvestment and directing distributions to the spending account.
• Pre-fund the first 5 years of the income gap with stable assets (CDs, Treasuries, money markets).
• Adopt a flexible spending rule so withdrawals can adjust in bad markets.

Helpful reading: Building a Withdrawal Strategy That Lasts

7Optimize your taxes

Withdrawals aren't taxed like paychecks. The order you draw from taxable, tax-deferred, and Roth accounts — and whether you use low-income years for Roth conversions — can change your lifetime tax bill by a surprising amount. The years right after retirement, before RMDs begin, are often the most valuable planning window of your life.

• Estimate how much of your retirement income will actually be taxable.
• Set a withdrawal order across taxable, tax-deferred, and tax-free accounts.
• Evaluate Roth conversions in your lower-income years using bracket-threshold planning.
• Plan withholding or estimated payments so April doesn't surprise you.
• If charitably inclined, look at donor-advised funds in a final high-income year and QCDs from age 70½.

Run the numbers: Roth Conversion Planner · Reading: The Break-Even Tax Rate

8Get your estate in order

An estate plan makes sure your wishes are carried out and spares your family confusion at the worst possible time. Beneficiary designations override your will, so this step is more than a document signing — it's an audit.

• Update your will, and confirm account titling and beneficiary designations match your wishes.
• Put advance medical directives and a durable financial power of attorney in place.
• Review any trusts and make sure you understand what each is for.
• Set up a password manager so someone can access your digital accounts.
• Check whether federal or state estate/inheritance taxes could apply to you.